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Table 3 Second-order reaction rate constant between unstrained olefin dienophiles with Fluorescein-Tetrazine

From: Tetrazine ligation for chemical proteomics

Entry Unstrained Olefin k (10−3 M−2 s−1)
1 prop-2-en-1-ol 9.4 ± 1.2
2 (E)-but-2-en-1-ol 1.9 ± 0.1
3 but-3-en-1-ol 26 ± 5
4 pent-4-en-1-ol 36 ± 4
5 2-(vinyloxy) ethan-1-ol 81 ± 1
6 (R)-N-(5-aminohexyl) acrylamide 1.2 ± 0.1
7 (R)-N-(5-aminohexyl) but-3-enamide 1.7 ± 0.2
8 (R)-N-(5-aminohexyl) pent-4-enamide 11 ± 2
9 (R)-N-(5-aminohexyl) hex-5-enamide 16 ± 1
10 (R,E)-N-(5-aminohexyl)-3-methoxyacrylamide 19 ± 1
  1. Fluorescein-Tetrazine = N-(2-(3-(3′,6′-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthen]-5-yl) thioureido) ethyl)-4-(1,2,4,5-tetrazin-3-yl) benzamide